Sweet flavor modifier

a technology of sweetener and sweetener, which is applied in the field of sweet flavor modifier, can solve the problems of delayed onset and lingering of sweetness, high-intensity sweeteners such as sucralose and aspartame, and report problems such as sweetness delivery problems

Active Publication Date: 2014-08-26
SENOMYX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0022]These and other embodiments, advantages, and features of the present invention are provided in the sections below. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

Problems solved by technology

Also, high intensity sweeteners such as sucralose and aspartame are reported to have sweetness delivery problems, i.e., delayed onset and lingering of sweetness (S. G. Wiet, et al., J. Food Sci., 58(3):599-602, 666 (1993)).

Method used

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examples

[0178]Having now generally described the invention, the same will be more readily understood by reference to the following examples, which are provided by way of illustration and are not intended as limiting. It is understood that various modifications and changes can be made to the herein disclosed exemplary embodiments without departing from the spirit and scope of the invention.

example a

4-amino-6-methoxyquinoline-3-carboxylic acid

[0179]

[0180]To a stirred solution of ethyl 4-amino-6-methoxyquinoline-3-carboxylate (Example Aa, 1.23 g, 5.0 mmol) in EtOH (20.0 mL) was added aqueous NaOH (2.0 N, 5.0 mL) at room temperature. The reaction mixture was then refluxed for 3 hr. The solution was then filtered and washed with water. The filtrate was cooled to 0° C. and neutralized carefully with 1 N HCl to pH 7. Most of the EtOH was removed under reduced pressure, and the precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as an off-white solid (1.01 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 3.89 (s, 3H), 7.40 (dd, J=2.8, 9.4 Hz, 1H), 7.73 (d, J=9.4 Hz, 1H), 7.77 (d, J=2.8 Hz, 1H), 8.77 (s, 1H). MS 219 (MH+).

example aa

ethyl 4-amino-6-methoxyquinoline-3-carboxylate

[0181]A mixture of ethyl 4-chloro-6-methoxyquinoline-3-carboxylate (Example Ab, 796 mg, 3.0 mmol) and ammonia (25% aqueous solution, 10 mL) in isopropanol (40 mL) was stirred at 110° C. in a pressure reactor overnight. Most of the solvent was then removed under reduced pressure, and the reaction mixture was diluted with water. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as an off-white solid (680 mg, 92%). 1H NMR (400 MHz, DMSO-d6) δ 1.33 (t, J=7.0 Hz, 3H), 3.88 (s, 3H), 4.32 (q, J=7.0 Hz, 2H), 7.36 (dd, J=2.8, 8.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.74 (d, J=2.8 Hz, 1H), 8.23 (bs, 2H), 8.77 (s, 1H). MS 247 (MH+).

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Abstract

The present invention includes compounds having structural formula (I), or salts or solvates thereof. These compounds are useful as sweet flavor modifiers. The present invention also includes compositions comprising the present compounds and methods of enhancing the sweet taste of compositions.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of priority to U.S. Provisional Application No. 61 / 522,806, filed Aug. 12, 2011 and entitled “SWEET FLAVOR MODIFIER”. This application is related to U.S. patent application Ser. No. 13 / 076,632, filed Mar. 31, 2011 and entitled “SWEET FLAVOR MODIFIER”, which claims the benefit of priority to U.S. Provisional Patent Application No. 61 / 320,528, filed Apr. 2, 2010 and entitled “SWEET FLAVOR MODIFIER”; and U.S. Provisional Patent Application No. 61 / 422,341, filed Dec. 13, 2010 and entitled “SWEET FLAVOR MODIFIER”. The contents of these applications are hereby incorporated by reference in their entireties for all purposes.FIELD OF THE INVENTION[0002]The invention relates to compounds suitable for modifying receptors and their ligands associated with chemosensory or chemosensory related sensation or reaction.BACKGROUND OF THE INVENTION[0003]The taste system provides sensory information about the chemical compo...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): A23L1/236A23L27/00A23L27/20A23L27/30
CPCA23L1/22091A23L2/60C07D215/54C07D451/06C07D401/12A23L1/22678A23L1/30C07D405/12A23L1/236A23V2002/00A61K47/22C07D215/42A23L27/30A23L27/88A61P1/00A61P3/00A61P3/04A61P43/00A61P3/10A61K31/4725C07D403/12C07D413/12
Inventor TACHDJIAN, CATHERINETANG, XIAO-QINGKARANEWSKY, DONALD S.SERVANT, GUYLI, XIAODONGZHANG, FENGCHEN, QINGZHANG, HONGDAVIS, TIMOTHY JAMESDARMOHUSODO, VINCENTWONG, MELISSA SUESELCHAU, VICTOR
Owner SENOMYX INC
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